


Undercover

by ChloeMac86



Category: Supernatural
Genre: Confused Castiel, Dean being a little shit, F/M, Fluff, Nudity, Sam being a bit of a Dom, Smut, Stripper Reader, Sweet Sam, UST, UST that gets resolved, drinking mention, sam being a sexy mofo
Language: English
Status: Completed
Published: 2016-10-30
Updated: 2016-10-30
Packaged: 2018-08-27 20:31:53
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,499
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8415679
Author URL: https://archiveofourown.org/users/ChloeMac86/pseuds/ChloeMac86
Summary: Reader goes undercover at a strip club to lure out an incubus. Sam and her have unresolved UST that gets well...resolved. Cameos by Dean and Castiel





	

Please come out of the bathroom, (Y/N).”

“No, not happening!”

“Why not?”

“I look like a slutty version of Britney Spears.”

“I’m sure you look fine, and we really need to get this job done. Please, come out of the bathroom.”

(Y/N) huffed in annoyance before saying, “Fine, but not one word, Samuel Winchester.”

(Y/N) walked out of the bathroom annoyed as all hell. An incubus just had to be working a strip club for victims. A fucking strip club. (Y/N) looked up when she heard the gasp come from in front of her. When she met Sam’s eyes, she found herself confused by the look in his eyes. It was an emotion she had never seen before, and she thought she was well-versed in Sam Winchester’s emotions. Rather than try and interpret the enigma of Sam Winchester, she just said, “Can we just go so we can get this over with?”

Sam looked dazed as he said, “Um…sure, let’s go.”

(Y/N) followed Sam out to the Impala. Dean was already at the club since he was working the club as a bouncer, but he hadn’t had any luck sniffing out the incubus so she had just gotten a job as dancer and tonight was her first night. They arrived at the club and she started to climb out of the car. Before she could, Sam grabbed her arm and said, “Are you sure you’re up for this, (Y/N)?”

Winking at Sam, she said, “I am always up for anything, Sammy,” before climbing out of the car and walking in the employee entrance. 

Sam sighed to himself before driving away to grab something to eat before the club opened to the public. 

******

(Y/N) was walking to the dressing room before she heard Dean call her name. She turned around, and said, “What? I need to finish getting ready.”

Dean looked her up and down appraisingly before saying, “Hot Damn. Has Sam seen this outfit?”

She looked at Dean like he had two heads, “Of course he did. He drove me here. Why?”

Dean smirked, “Please tell me he made a move.”

She looked confused, “What? A move? What are you talking about?”

“Darlin*, Sammy has had a thing for you since we met you.”

Trying to ignore the way her heart leapt at this statement she said, “No, he doesn’t. You’re crazy, Dean.”

Dean’s smirk got wider, “Hate to break it to you, doll, but I know my brother. He has the hots for you. Why do you think I never hit on you?”

(Y/N) smirked, “Because I can kick your ass?”

Dean frowned at her, “No, you can’t, and it was because I saw the look in his eye when he shook your hand for the first time.”

(Y/N) looked thoughtful for a minute and then said, “If that’s true, then make sure he sits as close to the stage as possible because I have a plan.”

Dean smirked, “I’ve always liked a girl who take charge.”

She smacked him playfully, “Dumbass. Now, go away. I have to get ready.”

Dean smirked for a second before he turned serious, “Sammy and I have your back, you know that right?”

(Y/N) smiled softly at the man who had become like a brother to her, “Yes, I know Dean.”

Dean coughed uncomfortably and she laughed, “Too much of a chick flick moment, Dean?”

Dean grumbled, “Yes.”

(Y/N) laughed harder and said, “Go. I need to get ready.”

Dean looked grateful as he turned tail and ran.

******

 

Sam shifted uncomfortably in his chair as his eyes scanned the strip club. For reasons unknown to him, Dean had told him he had to sit as close to the stage as possible. He was going to argue that sitting in the back allowed him a better vantage point, but Dean had had that stubborn look in his eye, and Sam knew it wasn’t worth the argument. The song currently playing ended, and the stripper who had been performing left the stage. The DJ then announced the next dancer, “Let’s welcome to the stage, Sapphire.”  
Sam found himself sitting up straighter as (Y/N) came out on stage. She was so beautiful he found himself thinking. He also began to realize the patrons of the club were going to see more of (Y/N) then he was strictly comfortable with. Suddenly, he realized he wasn’t as okay with this plan as he had initially thought. Focus, Sam, he told himself. They needed to get this incubus ganked before he killed anyone else, and he knew, logically, this was the best way. His heart just wasn’t enthused over the idea of using her as bait. However, he focused again as the beat of her song began. He groaned internally as he recognized the song, Me & You by Cassie.

As she began to dance, he realized this was not going to be easy. Where the hell had she learned to move like that? He found himself trying not to freak as she began unbuttoning the white button down she was wearing. However, the moment her shirt came off all the way, his breath hitched and his pulse spiked. She was wearing a pink lace bra that looked amazing against her skin. He had never seen so much of her skin before. Dean and Sam had both agreed from the get-go that (Y/N) would always get her own room, no matter what they had to do to pay for it. Now, he was really glad they had made that policy because if he had seen this much of her while sharing a motel room, he wasn’t sure he would have been able to keep his libido in check. Just seeing her bra and all the lovely bare skin of her stomach was making him have very bad thoughts. He was also white knuckling his chair to keep himself seated. He knew Dean and (Y/N) would not appreciate him storming the stage so he could drag her away to ravish her like some demented caveman. 

Sam began to take deep breaths to try to keep himself under control, but watching her work the pole like she did this every night was really testing Sam’s self-control. Then her skirt hit the stage exposing her pink thong and the lace at the top of the black and pink thigh highs she wore, and it took every ounce of self-control Sam possessed to stay seated so he wouldn’t blow the operation. Then she made eye contact with him as she sexily crawled to where he was sitting under the guise of making more tips. He pulled money out of his pocket to keep up the premise that he was a normal customer. She reached him, and his eyes nearly bugged out of his head as she unsnapped her bra dropping it beside her as she pushed her tits in his face as if he was a customer and she was a real stripper. She continued to press her boobs in his face as she stealthily whispered, “Our incubus is directly across the stage from you.”

He whispered back, “Got it. Make sure you get to him buy a lap dance after you come off stage.”

He nearly lost any shred of self-control he had left as she whispered, “When this is done, I owe you a lap dance, Mr. Winchester.”

He stuffed some bills in the strap of her thong before she turned and made her way over to entice the incubus for the duration of the song. As she made her way across to the target, Sam’s eyes were transfixed on her pert ass as he tried not groan from all the pent-up sexual tension.

******

 

(Y/N) signed in relief as she got in the back of the Impala. The incubus had fallen right into her honey trap, been ganked, and without her Sam, Dean, or her being seriously injured- just minor scrapes and bruises. However, as she locked eyes with Sam through the rearview mirror, she remembered what she had said to him while she was still on stage. She was actually amazed she had had the guts to do and say the things she had. Then she realized what emotion had been swirling in his eyes all night when he looked at her- lust. Suddenly, feeling bold, she found herself winking at Sam as he stared at her from the front seat of the Impala. She saw the lust darken in his eyes and decided she was definitely ready to see how things would play out with Sam. As she decided this, Dean pulled into the parking lot of the motel and said, “Who wants to hit a bar? I am too wound up to sleep.”

Faking a yawn, she made sure to lock eyes with Sam so he would get her unspoken message as she said, “No thanks, Dean. I have had enough of men ogling me for the night. I think I’m just going to watch a movie or something. What about you, Sam? Want to join me?”

Sam smiled and winked at her as he said, “I would love to join you, (Y/N). What movie did you want to watch?”

She smiled back at Sam as she said, “I’m not sure yet. I’m sure we’ll find something to do.”

Dean, obviously catching on to what Sam and her actually wanted to do, groaned, “Son of bitch, you two. I can smell the sexual tension from here.”

(Y/N) smirked sweetly at Dean as she said, “I have no idea what you are talking about, Dean. Do you, Sam?”

Sam smiled as he said, “Nope, no idea.”

Dean groaned again, “You two are really annoying, I’m going to the bar, and I’ll make Cas go with me. Cas! Get your feathered ass down here now.”

There was a small fluttering of wings before Castiel appeared, “Dean, my ass is not feathered.”

Dean groaned and shoved the angel towards the Impala, “You. Me. Bar. Now!”

As he got shoved towards the car, Cas did his patented head tilt as he said, “Aren’t Sam and (Y/N) going to come with us?”

“Nope, they have things to do, and I need to get blackout drunk so I forget this conversation ever happened.”

Castiel still looked confused, but got in the Impala anyway as Dean slid back into the driver’s side and cranked the engine back to life.Y/N ) smirked at Dean and lobbed one final parting shot, “I wouldn’t come back until the morning. The things I plan to do will take all night long.”

Dean groaned as he pulled out of the parking space and flipped the bird at both Sam and (Y/N) as the Impala left the motel parking lot. (Y/N) giggled before turning to Sam, slinging her arms around his waist, and whispering, “Hi, Sammy.”

Sam smiled down at her as he wrapped his own arms around her shoulders and said hi back to her. She suddenly found herself becoming shy again as she snuggled her face into Sam’s chest as she blushed realizing exactly what was going to happen tonight. Sam noticed her sudden shyness and used his hand to tilt her chin up so she was looking him the eye as he said, “Hey, we don’t have to do anything you aren’t ready for, okay? This isn’t about just sex to me. I care about you, and I want to be in a relationship with you.”

(Y/N) smiled as he said this feeling a renewed sense of confidence. She took Sam’s hand and guided him to her motel room. She opened the door to let them in, but once Sam closed the door, she pushed him up against it to kiss him. It took him a moment to get over the shock of her kissing him, but once he did, he was kissing her- really kissing her. It didn’t take long for the kiss to become heated as Sam lifted her up into his arms so she had to wrap her legs around his waist, her heels digging into his ass as they kissed. (Y/N) found herself working to get Sam out of his jacket and flannel at the same time which made her grumble, “Why do you Winchesters wear so many fucking layers?”

Sam laughed as he tried to help her while not having to put her down. He was finding he liked having her in his arms like this with those fucking heels digging into his ass. Those heels were definitely staying on for the main event. He loved how they made her legs look miles long and made her ass just look that much perkier. They finally managed to get his jacket and shirt off before (Y/N) realized something as Sam began to kiss her neck. She fought to get her brain back online because his lips were very distracting, but she finally managed to say, “As fun as this is, I still owe you that lap dance, Mr. Winchester.”

Sam all but growled out, “Are you trying to kill me?”

She smirked as she slid back down to the floor, “No, but I always keep my promises, Samuel.”

She then proceeded to push him until he finally sat in one of the chairs in the hotel room. She then walked over to her bag, grabbed her iPad and dock, and set them up. She scrolled through her playlist until she found the song she wanted. Before she hit play, she smirked at Sam as she said, “Now remember, the same rules applies as if this were a real club, no touching!”

Sam groaned as she giggled at him, “Now, I know you are trying to kill me.”

(Y/N) just continued to giggle as she said, “I promise that if you’re good and behave, your reward will be worth it.”

She then hit play as she turned towards Sam and began to unbutton her shirt as the opening notes of “Dance for You” by Beyoncé began to play. She began to walk towards him as she continued to unbutton her shirt. When she got right in front of Sam, she tossed her shirt aside and had to hide her smirk as his eyes darkened with lust. She then began to run her hands over his bare chest just letting herself enjoy the feel of his muscles rippling underneath them. She then straddled his lap as she began to roll her hips sensually to the song. She then pulled her hair out of the pigtails they had been in earlier as she shook her hair out. She noticed how Sam’s eyes seem to darken even more as she shook her hair out, and she had to bite back a giggle. She always forgot how much guys seemed to like watching a girl shake her hair out. She then began to do full body rolls against Sam which seemed to be having an effect as she felt something poke against her thigh. She really did smile as she got up off his lap for the moment. She also giggled slightly when she noticed that he was starting to reach for her before he remembered that he couldn’t touch her.

(Y/N) stood in front of him again then turned so her ass was facing him as she unzipped her skirt and let it fall as she bent over to really mess with him. Sam took in the view of her bent at the waist proudly showing off her ass exposed by her thong then let his eyes drift down to her legs encased by her lace thigh highs all the way down to her heels. He let out a growl as he realized she was unsnapping her bra. He watched as she dropped the bra to ground and turned back around, her arms shielding her breasts from his eyes. She finally dropped her arms as she walked back over to him and climbed back in his lap so her backside was pressed against his front. She then threw her arms back over his neck as she rolled her body letting him watch her almost fully exposed body. He nearly lost it when her hands came back down and began to knead her breasts. She then let her fingers walk down until they were hooked in her thong straps before ever so slowly taking her thong off. She lifted her hips slightly to get if off all the way, and before Sam knew it, (Y/N) was grinding on him fully nude except for the thigh highs and heels as the song came to an end. When the song ended, she stood back up from his lap and faced him as she crooked her finger while giving her bedroom eyes. Taking this as his cue that he could touch her again, he was up in a flash and before she could do anything else, she was back to being in Sam’s arms with her legs around his waist and his hands gripping her naked ass.

She put her mouth to his ear and licked the shell of it before he grabbed her jaw and pulled his lips to hers roughly. The kiss was rough and needy as they both fought for dominance, their tongues battling each other. Without warning or breaking the kiss, Sam lowered them to the bed so he was on top. He then unwrapped her legs from his waist and moved her legs apart so her pussy was bared to his hungry eyes. He then lowered himself so his mouth was next to (Y/N)’s ear as he purred, “The shoes and thigh highs are staying on.”

His voice sent a gush of wetness to her pussy as she moaned, “Ssss-aaa-mmm.”

Before she knew it, his lips and hands were everywhere, but the one place she wanted them most. She mewled in desperation which made him chuckle, the vibrations against her skin making her even wetter. Finally, when her body was buzzing with absolute need for this man, he finally put his mouth where she wanted it. He licked, kissed, and fucked her pussy with his mouth and tongue as his hands continued to knead her breasts. It seemed like only seconds had passed before she felt her orgasm begin to build inside her. Before she knew it, she was coming hard screaming his name.

Once she had come down from the high of her orgasm, she pulled herself to her knees on the bed, and pulled Sam up with her as she reached for his belt buckle. She had unbuckled his belt, undid his fly, and pulled his pants and boxer briefs down before he even knew what was happening. His hard cock sprung free, and (Y/N) gently took it her hand as she began to move her hand up and down his shaft making Sam moan her name. She used her other hand to push him back a little so she could get off the bed and kneel before him. Before she got all the way to her knees, Sam stopped her as he said, “Next time, gorgeous. I won’t last very long otherwise.”

Pouting her lower lip at him, she said, “Fine, but you better fuck me now with your cock, or I will not be held responsible for my actions.”

He smirked at her as he lowered her back to the bed before saying, “As you wish.”

He pulled her body so her pussy was at the edge of the bed and level with his cock. He slowly pushed into her inch by inch until he was fully sheathed in her pussy then groaned, “Fuck, so tight.”

Getting impatient, she growled, “Move, Mr. Winchester, NOW!”

Needing no further prompting, he slid back out slowly before slamming back in and setting a brutal pace. (Y/N) moaned an incoherent combination of ‘Fuck’, ‘Sam’, and ‘Harder’ as Sam slammed his cock in her pussy. Before she knew it, her second orgasm was building and before she knew it, she came hard with a final cry of “Sam!”

The orgasm was so intense her vision went white for a moment, but just as she started to see again, Sam was coming too with a loud cry of her name before collapsing on top of her. They both laid there for a minute just letting the adrenaline drain from their bodies. Once they were calm, Sam pulled himself up and moved to take her shoes and thigh highs off. Once they were off, he tucked her into the queen-sized bed before getting in next to her. He kissed her slowly for a few moments before pulling away and spooning her. He then kissed her forehead as he said, “Sleep, beautiful. We’ll talk in the morning.”

And with that, she fell asleep in Sam Winchester’s strong arms.


End file.
